(1S^∗,3R^∗)-3-amino-1-phenylbutane-1,4-diol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S^∗,3R^∗)-3-amino-1-phenylbutane-1,4-diol
• 英文别名: (1R,3S)-3-Amino-1-phenyl-1,4-butanediol；(1R,3S)-3-amino-1-phenylbutane-1,4-diol
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: ACQOCBCVBZQPAR-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-硝基苯基月桂酸酯 、 (1S^∗,3R^∗)-3-amino-1-phenylbutane-1,4-diol 以 二氯甲烷 为溶剂， 反应 168.0h， 以75%的产率得到N-((2S,4R)-1,4-dihydroxy-4-phenylbutan-2-yl)dodecanamide
  参考文献：
  名称：

  A domino Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines and application to the synthesis of the ceramide transport inhibitor (±)-HPA-12

  摘要：

  A Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines with primary and secondary amines has been developed which affords 4-hydroxy-3-aminoketones. The aza-Michael products were reduced using non-selective NaBH4/MeOH or diastereoselective (up to 92:8) SnCl4/NaBH4 conditions yielding (1R*,3S*)-3-amino-1,4-diols in up to 97% and 70% yield respectively. The major reduction product was converted in two steps to (+/-)-HPA-12, which is an inhibitor of the cytosolic ceramide transporting protein. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.11.010
• 作为产物：
  描述：

  buta-1,3-dien-1-ylbenzene 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 氢气 、 氧气 、 四氯化锡 、 Rose Bengal bis(tetrabutylammonium) salt 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 192.0h， 生成 (1S^∗,3R^∗)-3-amino-1-phenylbutane-1,4-diol
  参考文献：
  名称：

  A domino Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines and application to the synthesis of the ceramide transport inhibitor (±)-HPA-12

  摘要：

  A Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines with primary and secondary amines has been developed which affords 4-hydroxy-3-aminoketones. The aza-Michael products were reduced using non-selective NaBH4/MeOH or diastereoselective (up to 92:8) SnCl4/NaBH4 conditions yielding (1R*,3S*)-3-amino-1,4-diols in up to 97% and 70% yield respectively. The major reduction product was converted in two steps to (+/-)-HPA-12, which is an inhibitor of the cytosolic ceramide transporting protein. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.11.010

文献信息

• A domino Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines and application to the synthesis of the ceramide transport inhibitor (±)-HPA-12
  作者：Sarah V.A.-M. Legendre、Martyn Jevric、Julian Klepp、Christopher J. Sumby、Ben W. Greatrex

  DOI：10.1016/j.tet.2017.11.010

  日期：2018.3

  A Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines with primary and secondary amines has been developed which affords 4-hydroxy-3-aminoketones. The aza-Michael products were reduced using non-selective NaBH4/MeOH or diastereoselective (up to 92:8) SnCl4/NaBH4 conditions yielding (1R*,3S*)-3-amino-1,4-diols in up to 97% and 70% yield respectively. The major reduction product was converted in two steps to (+/-)-HPA-12, which is an inhibitor of the cytosolic ceramide transporting protein. (C) 2017 Elsevier Ltd. All rights reserved.